Trifluoroacetic acid → 3-(2-Oxo-2-(piperazin-1-yl)ethoxy)benzaldehyde

HRID 592076Notes

Reaction equation

HRID 592076 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)[O:6][CH2:7][C:8]([N:10]1[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]1)=[O:9])=[O:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:9]=[C:8]([N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[CH2:7][O:6][C:5]1[CH:4]=[C:3]([CH:25]=[CH:24][CH:23]=1)[CH:1]=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89725867Tert-Butyl 4-(2-(3-formylphenoxy)acetyl)piperazine-1-carboxylate2×

Product 1

HCID 897262023-(2-Oxo-2-(piperazin-1-yl)ethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl 4-(2-(3-formylphenoxy)acetyl)piperazine-1-carboxylate (49)/(5.55 mmol) was taken in DCM and cooled to 0° C. when TFA (5 ml) was added drop wise and then stirred at rt for 16 h when TLC confirmed completion of reaction. The reaction mixture was concentrated and neutralized with satd NaHCO3 solution followed by extraction with DCM. The combined organic extracts was dried, concentrated and used directly for the next step (86%). LCMS: 98.12% (M++1).

Workup

  1. additionwas added drop wise
  2. customcompletion of reaction
  3. concentrationThe reaction mixture was concentrated
  4. extractionfollowed by extraction with DCM
  5. customThe combined organic extracts was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c18d9be70abe4cc89c3413b3ee5ddc00
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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